Jack Allan cannot count the number of times he's been approached with invitations beginning something like, "My sister has a friend…" It seems as if everyone in the small town of Corbett, Idaho, is intent on finding a wife for him—everyone except for Jack himself. The townspeople gossip that this is because Jack, a young widower, has not gotten over the death of his wife, Katelin, and in a way they are right. However, it isn't his undying love for Katelin which is holding Jack back. Rather it is the memory of events surrounding her death, events about which only he knows and which have left him filled with guilt.

Undeterred, Ruby Henderson, Jack's feisty neighbor, introduces him to her granddaughter, Ally. Jack unwittingly finds himself attracted to Ally, and it seems she is attracted to him too. So he is stunned when he finally asks her out and she turns him down his by saying it would be best if they were just friends. This sets in motion events which lead Jack into one romantic entanglement after another and with not one possible romantic interest but three.

Set against the backdrop of farming and small town life, The Reluctant Courtship of Jack Allan is filled with amusing characters. It tells a story which is sometimes humorous and sometimes poignant as Jack struggles with his guilt while also working to sort out his love life and those of the people around him.